AAAAAAAAAAARYL HALIDES PRESENTATION.pptx

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1. ARYL HALIDES SUNNY E. AMAR DIANE L. CELESTIAL ELBERT B. LASERNA Demonstrators

2. I. OBJECTIVES At the end of the lesson, the students should be able to:   a. Discuss Aryl Halides and its example; b. Describe the physical and chemical properties of Aryl Halides; c. Examine the chemical reactions associated with Aryl Halides; d. Write the name and structure of Aryl Halides; and Identify Aryl Halides found in living organisms.

3. KEYTERMS Benzene – a colorless volatile flammable toxic aromatic hydrocarbons C6H6 used in organic synthesis, as solvent, and as motor fuel. Benzene ring – a structural arrangement of atoms in benzene and other aromatic compounds that consists of planar symmetrical hexagon of six carbon atoms which derives added stability from the delocalization of certain bonding electrons over the entire ring

4. Halides - a binary compound of a halogen with a more electropositive element or radical. Halogens – any of the four elements fluorine, chlorine, bromine, and iodine that form part of group VIIA of the periodic table and exist in free state normally as diatomic molecules.

5. 1. ARYL HALIDES The word  aryl  means aromatic (benzene) ring and the word  halide  means a halogen of some sort: fluorine, chlorine, bromine, or iodine. When you're looking at an  aryl halide , it's simply one of the four halogen atoms bonded directly to a benzene ring.

6. Aryl halides have the general formula ArX , where ( Ar -) is phenyl or substituted phenyl and (X) is F, Cl , Br, and I.

7. Examples of Aryl Halides

8. 2. PHYSICAL PROPERTIES OF ARYL HALIDES   Aryl halides resemble alkyl halides in many of their physical properties. All are practically insoluble in water and most are denser than water. Melting points and boiling point for some representative aryl halides. Aryl halides are polar molecules but are less polar than alkyl halides.

9. Other properties in Aryl Halides Aryl halides are compounds in which a halogen substituent is attached directly to an aromatic ring.  

10. Sources of Aryl Halides The two principal methods for the preparation of aryl halides- direct halogenation of arenes by electrophilic aromatic substitution and preparation by way of aryldiazonium salts.

11. There are halogen containing aromatic compounds that are widely dispersed in the environment and the most familiar example is 1,1,1-trichloro-2,2-bis(p- chlorophenyl )ethane, or  DDT .

12. Natural occurrence Many organohalogen compounds in which the  halogen  is directly attached to a benzenoid ring occur naturally. Unlike alkyl and vinylic halides, for which marine origins are the most common, aryl halides are found in a variety of sources.  L - Thyroxine , for example, is an iodine-containing  amino acid  secreted by the  thyroid gland  that acts as a regulator of  metabolism . At one time, natural  L - thyroxine extracted from the thyroids of animals was used to treat patients with thyroxine deficiencies, but today almost all of the  L - thyroxine used to treat thyroid disorders is synthetic.  

13. REACTIONS IN ARYL HALIDES   1. Halogenation of arenes . Aryl chlorides and bromides are conveniently prepared by electrophilic aromatic substitutions. The reaction is limited to chlorination and bromination . Fluorination is difficult to control;iodination is too slow to be useful.

14. 2. The Sandmeyer Reaction. Diazotization of a primary arylamine followed by treatment of the diazonium salt with copper(I) bromide or copper(I) chloride yields the corresponding aryl bromide or aryl chloride.

15. 3. The Schieman reaction. Diazontization of an arylamine followed by treatment with flourobic acid gives an aryl diazoniumflouroborates salt. Heating this salt converts it to aryl fluoride.

16. 4. Reaction of Aryl diazonium salts with iodide ion. Adding potassium iodide to solution of an aryl diazonium ion lead to the formation of an aryl iodide.

17. 4. Related to living things: Griseojulvin : Biosynthetic product of a particular microorganism, used as an orally administered antifungal agent.

18. Dibromoindigo : principal constituent of a dye known as Tyrian purple, which is isolated from a species of Meditarranean sea snail and was much prized by the ancient for its vivid color.  

19. Chlortetracycline: is a tetracycline antibiotic, and historically the firstt member of this class to be indentifying. It was discovered in 1945, by the scientist, Bejamin Minge Duggar , working at Lenderle laboratories under the Supervisions of Yellapragada Subbarow .

20. Maytansine : a potent antitumor agent isolated from a bush native to Kenya; 10 tons plant yieided 6 g of maytansine .

21. 5. Nomenclature of Aryl Halides Function groups prefix = halo- Function groups suffix = -benzene It means that halogens such as Fluorine (F), Chlorine ( Cl ), Bromine (Br) and Iodine (I) attached to the benzene ring.

22. Drop the “ ine ” and replace with “o” and add the suffix benzene. Example Result Fluorine = Fluoro + benzene Fluorobenzene Chlorine = Chloro + benzene Chlorobenzene Bromine = Bromo + benzene Bromobenzene Iodine = Iodo + benzene Iodobenzene

23. Numbering of the ring begins at the halogen-substituted carbon and proceeds in the direction of the next substituted carbon that possesses the lower number. 1-Chloro-2-nitrobenzene 1-Chloro-2,3-dinitrobenzene

24. Ortho, Meta or Para? Mono-substituted aryl halides are characterized using the prefix ortho ( o- ), meta ( m- ) or para ( p- ) depending on the placement of the substituent from the halogen or the halogen from a higher priority functional group: 1,2-, 1,3- or 1,4- respectively.  Example: 1-chloro-2-ethylbenzene  or   o - ethylchlorobenzene 1-chloro-3-ethylbenzene  or   m - ethylchlorobenzene 1-chloro-4-ethylbenzene  or   p - ethylchlorobenzene

25. 1-chloro-3-ethylbenzene  or   m - ethylchlorobenzene 1-chloro-2-ethylbenzene  or   o - ethylchlorobenzene

26. Some Example of Aryl Halides

27. Is it an example of Aryl Halides? Benzyl Chloride

28. Note: Any halogen compound that contains a benzene ring is not classified as aryl halide. e.g. Benzyl chloride is not an aryl halide, its halogen is not directly attached to the aromatic ring but it is a substituted alkyl halide.  

29. Thank You For Listening……. Lets Move on to the Application